CA2902992C - Composes de rhodamine et leur utilisation comme marqueurs fluorescents - Google Patents

Composes de rhodamine et leur utilisation comme marqueurs fluorescents Download PDF

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Publication number
CA2902992C
CA2902992C CA2902992A CA2902992A CA2902992C CA 2902992 C CA2902992 C CA 2902992C CA 2902992 A CA2902992 A CA 2902992A CA 2902992 A CA2902992 A CA 2902992A CA 2902992 C CA2902992 C CA 2902992C
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Canada
Prior art keywords
alkyl
group
compound
nucleotide
substituted
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CA2902992A
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English (en)
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CA2902992A1 (fr
Inventor
Nikolai Nikolaevich Romanov
Xiaohai Liu
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Illumina Cambridge Ltd
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Illumina Cambridge Ltd
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Publication of CA2902992A1 publication Critical patent/CA2902992A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Genetics & Genomics (AREA)
  • Immunology (AREA)
  • Physics & Mathematics (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Cell Biology (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

La présente invention concerne de nouveaux composés de rhodamine et leur utilisation comme marqueurs fluorescents. Les composés peuvent être utilisés comme marqueurs fluorescents de nucléotides dans des applications de séquençage d'acide nucléique.
CA2902992A 2013-03-08 2013-03-08 Composes de rhodamine et leur utilisation comme marqueurs fluorescents Active CA2902992C (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2013/054793 WO2014135223A1 (fr) 2013-03-08 2013-03-08 Composés de rhodamine et leur utilisation comme marqueurs fluorescents

Publications (2)

Publication Number Publication Date
CA2902992A1 CA2902992A1 (fr) 2014-09-12
CA2902992C true CA2902992C (fr) 2020-08-25

Family

ID=47882139

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2902992A Active CA2902992C (fr) 2013-03-08 2013-03-08 Composes de rhodamine et leur utilisation comme marqueurs fluorescents

Country Status (7)

Country Link
EP (1) EP2964624B1 (fr)
CN (1) CN105263918B (fr)
AU (1) AU2013380647B2 (fr)
CA (1) CA2902992C (fr)
DK (1) DK2964624T3 (fr)
ES (1) ES2620427T3 (fr)
WO (1) WO2014135223A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201414098D0 (en) 2014-08-08 2014-09-24 Illumina Cambridge Ltd Modified nucleotide linkers
WO2016065248A1 (fr) 2014-10-23 2016-04-28 Complete Genomics, Inc. Séquençage de confinement de signal (sc) et analogues de nucléotides utiles pour le séquençage de confinement de signal
CN107459482B (zh) * 2016-06-03 2020-11-17 华东理工大学 一氧化氮供体、其制备及应用
US10385214B2 (en) 2016-09-30 2019-08-20 Illumina Cambridge Limited Fluorescent dyes and their uses as biomarkers
EP4257596A3 (fr) * 2016-12-22 2023-12-06 Illumina Cambridge Limited Composés coumarines et leurs utilisations en tant que marqueurs fluorescents
GB201711219D0 (en) * 2017-07-12 2017-08-23 Illumina Cambridge Ltd Short pendant arm linkers for nucleotides in sequencing applications
CN114656499B (zh) * 2020-12-24 2026-04-21 郑州思昆生物工程有限公司 一种硅基罗丹明化合物及其制备方法、荧光修饰核苷酸、试剂盒
CN114671842B (zh) * 2020-12-24 2024-05-28 郑州思昆生物工程有限公司 一种荧光化合物及其制备方法、荧光修饰核苷酸、试剂盒
CN114671843B (zh) * 2020-12-24 2023-07-04 郑州思昆生物工程有限公司 一种荧光化合物、荧光修饰核苷酸、试剂盒
US12359068B2 (en) * 2023-02-10 2025-07-15 Singular Genomics Systems, Inc. Rhodamine fluorescent compounds and production methods thereof

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB517097A (en) 1937-12-10 1940-01-19 Adrianus Kleijn An improved apparatus for testing the quality of grain and flour
US5268486A (en) 1986-04-18 1993-12-07 Carnegie-Mellon Unversity Method for labeling and detecting materials employing arylsulfonate cyanine dyes
US5302509A (en) 1989-08-14 1994-04-12 Beckman Instruments, Inc. Method for sequencing polynucleotides
US5846719A (en) 1994-10-13 1998-12-08 Lynx Therapeutics, Inc. Oligonucleotide tags for sorting and identification
JP2002503954A (ja) 1997-04-01 2002-02-05 グラクソ、グループ、リミテッド 核酸増幅法
US6465178B2 (en) 1997-09-30 2002-10-15 Surmodics, Inc. Target molecule attachment to surfaces
US6485944B1 (en) 1997-10-10 2002-11-26 President And Fellows Of Harvard College Replica amplification of nucleic acid arrays
WO2000006770A1 (fr) 1998-07-30 2000-02-10 Solexa Ltd. Biomolecules en rangees et leur utilisation dans une procedure de sequençage
GB0002310D0 (en) 2000-02-01 2000-03-22 Solexa Ltd Polynucleotide sequencing
AR021833A1 (es) 1998-09-30 2002-08-07 Applied Research Systems Metodos de amplificacion y secuenciacion de acido nucleico
US6391937B1 (en) 1998-11-25 2002-05-21 Motorola, Inc. Polyacrylamide hydrogels and hydrogel arrays made from polyacrylamide reactive prepolymers
US6664061B2 (en) 1999-06-25 2003-12-16 Amersham Biosciences Ab Use and evaluation of a [2+2] photoaddition in immobilization of oligonucleotides on a three-dimensional hydrogel matrix
US6372813B1 (en) 1999-06-25 2002-04-16 Motorola Methods and compositions for attachment of biomolecules to solid supports, hydrogels, and hydrogel arrays
WO2002012566A2 (fr) 2000-08-09 2002-02-14 Motorola, Inc. Utilisation et evaluation d'une photocycloaddition [2+2] dans une immobilisation d'oligonucleotides sur une matrice hydrogel tridimensionnelle
EP1322710B2 (fr) 2000-09-29 2015-02-18 Life Technologies Corporation Colorants carbocyanines modifies et leurs conjugues
ES2864086T3 (es) 2002-08-23 2021-10-13 Illumina Cambridge Ltd Nucleótidos etiquetados
EP3002289B1 (fr) 2002-08-23 2018-02-28 Illumina Cambridge Limited Nucleotides modifies pour le sequençage de polynucleotide
DE10258150A1 (de) 2002-12-10 2004-07-08 Dyomics Gmbh Hydrophile Marker auf der Basis von Benzopyrylo-Polymethinen
GB0321306D0 (en) 2003-09-11 2003-10-15 Solexa Ltd Modified polymerases for improved incorporation of nucleotide analogues
GB0326073D0 (en) 2003-11-07 2003-12-10 Solexa Ltd Improvements in or relating to polynucleotide arrays
EP1701785A1 (fr) 2004-01-07 2006-09-20 Solexa Ltd. Reseaux moleculaires modifies
WO2006120433A1 (fr) 2005-05-10 2006-11-16 Solexa Limited Polymerases ameliorees
GB0517097D0 (en) 2005-08-19 2005-09-28 Solexa Ltd Modified nucleosides and nucleotides and uses thereof
CN101454315B (zh) * 2006-03-31 2016-08-17 应用生物系统有限责任公司 用于合成罗丹明-标记的寡核苷酸的试剂
US8178360B2 (en) 2006-05-18 2012-05-15 Illumina Cambridge Limited Dye compounds and the use of their labelled conjugates
US8951938B2 (en) * 2007-12-20 2015-02-10 New York University Combinatorial rosamine library to detect cell-state switching
WO2010033011A1 (fr) * 2008-09-19 2010-03-25 Cancer Research Initiatives Foundation Dérivés de rosamine comme agents pour le traitement d'un cancer

Also Published As

Publication number Publication date
DK2964624T3 (en) 2017-04-03
AU2013380647B2 (en) 2017-05-04
CN105263918B (zh) 2018-05-18
EP2964624B1 (fr) 2017-01-04
WO2014135223A1 (fr) 2014-09-12
CN105263918A (zh) 2016-01-20
HK1218751A1 (en) 2017-03-10
HK1216642A1 (zh) 2016-11-25
ES2620427T3 (es) 2017-06-28
AU2013380647A1 (en) 2015-10-01
EP2964624A1 (fr) 2016-01-13
CA2902992A1 (fr) 2014-09-12

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